2-methylthio-4-(2'-naphthyl)-1-azetine | 1352447-80-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methylthio-4-(2'-naphthyl)-1-azetine
• CAS: 1352447-80-3
• 化学式: C₁₄H₁₃NS
• 分子量: 227.33
• InChiKey: SKGOFMKWSWIMGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-methylthio-4-(2'-naphthyl)-1-azetine 、 二苯基环丙烯酮 以 乙腈 为溶剂， 以51%的产率得到5-methylthio-2,3-diphenyl-7-naphthyl-1-azabicyclo[3.2.0]hept-2-en-4-one
  参考文献：
  名称：

  Pyridines from Azabicyclo[3.2.0]hept-2-en-4-ones through a Proposed Azacyclopentadienone

  摘要：

  Pyridines have been formed by heating azabicyclo[3.2.0]hept-2-en-4-ones in toluene. The generation of a 3-azacyclopentadienone intermediate via a [2 + 2]-cycloreversion Is proposed as the key step. A Diels-Alder reaction of a styrene, extrusion of carbon monoxide, and loss of hydrogen then gives the pyridine. The process parallels the well-known synthesis of benzenes from cyclopentadienones. The azabicyclo[3.2.0]hept-2-en-4-ones were synthesized from the reaction between readily available cyclopropenones and 1-azetines, In which the cyclopropenones behave as all-carbon 1,3-dipolar equivalents.

  DOI：

  10.1021/ol202924s
• 作为产物：
  描述：

  2-乙烯基萘 在 劳森试剂 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.67h， 生成 2-methylthio-4-(2'-naphthyl)-1-azetine
  参考文献：
  名称：

  Pyridines from Azabicyclo[3.2.0]hept-2-en-4-ones through a Proposed Azacyclopentadienone

  摘要：

  Pyridines have been formed by heating azabicyclo[3.2.0]hept-2-en-4-ones in toluene. The generation of a 3-azacyclopentadienone intermediate via a [2 + 2]-cycloreversion Is proposed as the key step. A Diels-Alder reaction of a styrene, extrusion of carbon monoxide, and loss of hydrogen then gives the pyridine. The process parallels the well-known synthesis of benzenes from cyclopentadienones. The azabicyclo[3.2.0]hept-2-en-4-ones were synthesized from the reaction between readily available cyclopropenones and 1-azetines, In which the cyclopropenones behave as all-carbon 1,3-dipolar equivalents.

  DOI：

  10.1021/ol202924s

文献信息

• 1,2,4-Oxadiazoles from cycloreversions of oxadiazabicyclo[3.2.0]heptenes: 1-azetines as thiocyanate equivalents
  作者：Karl Hemming、Musharraf N. Khan、Paul A. O'Gorman、Arnaud Pitard

  DOI：10.1016/j.tet.2012.12.007

  日期：2013.1

  1,3-Dipolar cycloaddition of nitrile oxides to 4-aryl-2-alkylthio-1-azetines gave a series of oxadiazabicyclo[3.2.0]heptenes as single diastereoisomers. Heating these cycloadducts in toluene resulted in an overall [2+2]-cycloreversion to give 5-alkylthio-3-aryl-1,2,4-oxadiazoles. In this process, the 1-azetine behaves as a thiocyanate equivalent. When the nitrile oxide substituent was 2-azidobenzene, the azide could be converted into a 1,2,3-triazole giving a (1,2,4-oxadiazolo)-(1,2,3-triazolo)-1,2-disubstituted benzene. 1,2,4-Oxadiazoles are sought after in medicinal chemistry and materials sciences. (c) 2012 Elsevier Ltd. All rights reserved.